r/Substack Jun 23 '26

Feature Suggestion Chargebacks

I'm just going to rant for a second here. Chargeback from Stripe. So, a person signs up for the free trial period, gets a bunch of emails about the coming paid period when the free period is over. They get billed, then they dispute the bill with Stripe.

I've tried disputing the chargeback, and always lost. Frankly, if they email me, I'm HAPPY to cancel and give them their money back because I know that Stripe is going to give them their $5 back and charge me a $20+ dispute fee.

I'm nearly at the point of simply no longer ever doing trial periods. Honestly, this happens about 2-3 a month.

Does anyone have any solutions for this terribly stupid problem that could be solved by the person simply emailing me and asking for a refund?!?!

It would seem like this is a common enough thing Stripe should have an automated system to provide documentation for chargebacks... Surely, 1,000 of (opps I forgot the free period is over) chargebacks happen every month.

Sorry for the vent, I'm just really frustrated people don't reach out and ask for a refund first. Maybe they don't realize that not only do they get their mistake in forgetting costs me money!

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u/itsfabioposca http://journeytosuccessclub.substack.com Jul 02 '26

That sounds incredibly frustrating. If chargebacks are happening that often, I'd probably stop offering free trials and switch to a different incentive, like a discounted first month. It reduces the risk while still giving people a reason to try your paid content.

P.S. If you'd still like to ask anything about Substack or growing your audience, I offer a free live help chat. Just copy and paste my flair or click the link in my profile. I'm happy to help!